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JohannesDahlstrom comments on Contrived infinite-torture scenarios: July 2010 - Less Wrong
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How would it even be possible to have sex with the mermaid with the fish bottom? I don't even know if that would work. Anyway, I'd pick the human bottom.
FWIW, one way to solve this problem would be to postulate mermaids to be marine mammals (they do have a placental umbilicus and mammaries after all in most depictions...), so their bottom part would be more akin to that of a dolphin, not a fish.